Owner Direct Family Rentals in Calheta

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  2. Family Friendly Rentals
  3.  Portugal

  4.  Madeira Region

  5.  Calheta

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1199 Calheta Family Rentals From $60

Organizing a family trip to Calheta? Discover large vacation rentals designed with plenty of room for group dining and recreation. Owner Direct lists verified multi-bedroom properties so the whole family stays comfortable.

Refúgio do Santa
Refúgio do Santa
House
Calheta, Madeira Region, Portugal
0.2k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
9.4

Superb

7 reviews

$116
Average price / night
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STONE HOUSE
STONE HOUSE
Cottage
Lombo do Doutor, 9370, Portugal
0.1k from Calheta center

AC, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$164
Average price / night
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Casa Miradouro do Pigarro, Sunny Apartment
Casa Miradouro do Pigarro, Sunny Apartment
Apartment
Calheta, Portugal
0.2k from Calheta center

Air Conditioner, Balcony/Terrace, Parking, View, Security/Safety, Child Friendly

1 Bedroom3 Guests
9.1

Superb

25 reviews

$88
Average price / night
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VIEWPOINT HOUSE
VIEWPOINT HOUSE
Cottage
Calheta, 9370-173, Portugal
0.2k from Calheta center

AC, Balcony, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$207
Average price / night
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Marina View Apartment - Pool & stunning ocean view
Marina View Apartment - Pool & stunning ocean view
Apartment
Portugal
0.2k from Calheta center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
9.8

Exceptional

11 reviews

$259
Average price / night
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Luxury Villa Pérola
Luxury Villa Pérola
House
Calheta, 9370-179, Portugal
0.3k from Calheta center

AC, Balcony, Crib, Fitness Equipment, Free Parking, Heater, Internet, Laundry, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$579
Average price / night
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Lombo do Doutor Cottage 1 by Mth
Lombo do Doutor Cottage 1 by Mth
House
Portugal
0.3k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

1 Bedroom3 Guests
8.7

Fabulous

20 reviews

$133
Average price / night
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Casa Félix, Calheta: Villa with unique view! Private Pool!
Casa Félix, Calheta: Villa with unique view! Private Pool!
House
Madeira, 9370-765, Portugal
0.3k from Calheta center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

144 reviews

$276
Average price / night
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Lombo do Doutor Cottage 2 by Mth
Lombo do Doutor Cottage 2 by Mth
House
Portugal
0.3k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

1 Bedroom3 Guests
8.0

Good

22 reviews

$136
Average price / night
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Luxury Villa with private pool, beautiful ocean views and mountain
Luxury Villa with private pool, beautiful ocean views and mountain
Villa
calheta, 9370-763, Portugal
0.4k from Calheta center

Balcony, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms4 Guests
9.8

Exceptional

84 reviews

$197
Average price / night
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Marina Rooms
Marina Rooms
House
Calheta, Portugal
0.3k from Calheta center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Beach

5 Bedrooms12 Guests
7.8

Good

330 reviews

$239
Average price / night
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Holiday Home 'Calheta Beach House T2' with Mountain View, Private Terrace and Wi-Fi
Holiday Home 'Calheta Beach House T2' with Mountain View, Private Terrace and Wi-Fi
House
Lombo Do Doutor, 9370-135, Portugal
0.4k from Calheta center

Barbecue, Extra Bed, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
8.0

Good

1 reviews

$420
Average price / night
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O Meu Sonho
O Meu Sonho
House
Portugal
0.3k from Calheta center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
9.4

Superb

68 reviews

$60
Average price / night
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Cliff House
Cliff House
Cottage
Lombo do Doutor, 9370, Portugal
0.5k from Calheta center

Balcony, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$202
Average price / night
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Sky & Ocean Villa
Sky & Ocean Villa
Villa
Calheta, Portugal
0.4k from Calheta center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms16 Guests
8.8

Fabulous

46 reviews

$426
Average price / night
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Casa Agrela , 36547/AL A beautiful warm home even in the Winter months
Casa Agrela , 36547/AL A beautiful warm home even in the Winter months
Villa
Estreito Da Calheta, 9370-763, Portugal
0.5k from Calheta center

Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$338
Average price / night
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Casa da Praia Calheta - Moradia
Casa da Praia Calheta - Moradia
House
Calheta, 9370-135, Portugal
0.5k from Calheta center

AC, Balcony, Barbecue, Crib, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$218
Average price / night
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White Rabbit II by Madeira Sun Travel
White Rabbit II by Madeira Sun Travel
Ski Chalet
Calheta, 9370-765, Portugal
0.6k from Calheta center

AC, Balcony, Crib, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$166
Average price / night
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Calheta Hills I – With pool and sea view
Calheta Hills I – With pool and sea view
Apartment
Calheta, 9370, Portugal
0.6k from Calheta center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$824
Average price / night
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Calheta Hills II – Relax with Sea View and Pool
Calheta Hills II – Relax with Sea View and Pool
Apartment
Estreito da Calheta, 9370-153, Portugal
0.7k from Calheta center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$828
Average price / night
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Calheta Hills III – Modern Retreat with Sea View
Calheta Hills III – Modern Retreat with Sea View
Apartment
Calheta, 9370, Portugal
0.7k from Calheta center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave

1 Bedroom3 Guests
10.0

Exceptional

2 reviews

$504
Average price / night
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Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Friendly Rentals in Calheta.

Where to stay in Calheta? Best neighborhoods & areas

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OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Calheta Family Friendly Rentals on the Map

Why Travelers Love Using Owner Direct to
Find Austin Family Friendly Rentals

What makes our family friendly rentals stand out?

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Verified Properties

Every family friendly rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Calheta. If you plan on staying in the Calheta area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Calheta

You can explore 1199 verified family-friendly vacation rentals in Calheta. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Calheta vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $60 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Calheta offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it's helpful to check the listing details before booking.

Yes, some rentals in Calheta are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Calheta often include amenities such as Child Friendly, Balcony/Terrace, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.